Chet Baker was a no show. The trumpeter and singer was slated to perform at a concert in Laren, Holland, which was being broadcast live across Europe.

Baker was meant to share the billing that night with the tenor player Archie Shepp. It was an odd pairing to say the least. Shepp was an incendiary performer, pushing the outer boundaries of free jazz. Baker, once the epitome of the cool west coast sound, had scarcely changed his playing style in 30 years. Two hours before the show, the producer went to Baker’s hotel room to collect the musician and drive him to the venue. Baker wasn’t there.

A frantic search ensued. There was no trace of Baker in his usual haunts. Even his dealers in the Zeedijk shooting galleries hadn’t seen him.

Baker rarely missed a gig. He was too desperate for the money. His habit had grown to an almost surreal level. In that spring of 1988, Chet was shooting six grams of high-grade heroin a day. He had run out of veins to shoot in, so he had taken to injecting himself in his scrotum. He backed his heroin fixes with long lines of cocaine. His days had been fueled by one big speedball after another.

Finally, Baker’s Alfa Romeo pulled up at the concert hall. But Baker wasn’t in the sports car. It was driven by one of his dealers, Bob Holland. Holland had been looking to score some drugs for Baker, but he hadn’t seen the trumpeter in two days. Holland said Baker had been “out of his mind” the last time he saw him, tormented by the fact that his girlfriend, Diane Vavra, after one too many beatings, had left him for good.

“Bob, I’m 58 years old,” the cadaverous Baker, preparing to inject himself in his crotch, told Holland a few days before he died. “I’ve used this stuff for thirty years. You can’t help me. I’m too far out.”

* * *

Chet Baker was laying in a fetal position on the sidewalk outside a cheap hotel near Amsterdam’s Central Train Station when police found his body. Blood covered his face and coated his blue-striped pants. His skull was crushed. It was 3:30 in the morning. The moon was full.

At the scene, the police made a judgment that the dead man had jumped out of a window in the Prins Hendrik Hotel, hitting his head on a concrete street post. There was no identification on the body, which was duly wrapped in a white cloth and sent to the morgue.

The next morning Dutch police returned to the Prins Hendrick Hotel to investigate. They soon determined that a room about 30 feet above where the body had been found had been rented by a Chet Baker. The name was not familiar to the police detectives.

The small room was locked from the inside. After entering, police found two glasses: one with a hypodermic needle containing a gram of heroin and another with a mixture of heroin and cocaine. They also discovered a small satchel containing a trumpet, a bracelet, a lighter and a few coins.

The Dutch police assumed that the anonymous corpse was just another junkie suicide. The small window only opened a few inches wide, just enough to permit the spectrally thin Baker to slither through for the final plunge.

Even though conspiracy theories would soon begin to take root, the cops were almost certainly right—though this was no ordinary addict. Give or take William Burroughs, Chet Baker was at the time of his death the world’s most notorious and unrepentant heroin fiend. He was also, for a few years in the 1950s, the most popular jazz trumpeter in the world, playing with a delicate, almost ethereal lyricism.

* * *

In 2002 James Gavin published his excruciatingly detailed biography of Chet Baker, Deep in a Dream: the Long Night of Chet Baker. (After 16 years, the book is finally available in paperback.) Gavin slices through the shroud of mystique that has enveloped Baker since his emergence as the personification of white cool in 1953. Gavin reveals Baker to be a timid and passive-aggressive personality, a deeply insecure musician, who often didn’t understand the structure of the songs he was playing. Even so, some of Baker’s records are undeniably beautiful, featuring an eerie noirish quality, the sound of American ennui. He was a genuine and unique talent, capable of reducing a song to its melodic core. He was the great minimalist of post-bebop jazz, though Baker himself may not have even appreciated the term. Gavin repeatedly refers to him as something of an idiot savant, a natural talent, even though the range of his genius was extremely narrow.

Deep in a Dream (the title is taken from an otherworldly Baker song from the late 1950s) is surely one of the most harrowing biographies ever written, an unrelenting and merciless account of the musician as junkie. The reading experience is exhausting and claustrophobic, something akin to squirming through Pier Paolo Pasolino’s Salo: 120 Days of Sodom.

Much of Baker’s life after 1958 is spent chasing the next high and doing almost anything to get it, from selling his trumpet to stealing drugs, money and prescriptions to using his many girlfriends and wives to run drugs for him, often at great risk to their own safety. Gavin renders the contours of Baker’s descent in prose as stark and austere as one of Baker’s own songs. Here’s Gavin’s description of the night when Baker forced his girlfriend Sandy Jones to shoot up with high grade heroin and left her alone in a comatose state:

Starting with his mother, Baker’s feelings about women had always been violently ambivalent: he needed them, yet he hated them for it. Jones became his latest victim. Years later she recounted the time “Chet tried to kill me.” In fact, it happened twice, although she never understood why. One day he came to the apartment with “a whole out fit of the darkest stuff in the world.” He shoved her into the bathroom, cooked up the dope, tied her arm, and plunged in a needle. “I got weak in the knees,” she said. “A couple of days later I came to.” She learned that Baker had walked out, leaving her on the floor – “blue, blue, blue.”

Chet Baker is a repellent figure, too coarse and pathological to be considered tragic. He was the ultimate nihilist. As a doper, he makes Keith Richards look like a novice. He seems to have had little curiosity about his condition, and even less empathy for the dozens of other lives he helped to wreck, including those of his children. When his son Dean was hit by a truck and seriously injured, Baker didn’t even call to check on his condition. Still Gavin’s account is strangely sympathetic. Baker lived moment to moment, fix to fix, gig to gig. And yet he was able, even in a heroin haze, to play some of the most unforgettable melodies in jazz, tunes that continue to haunt the mind long after his death.

* * *

Chesney “Chet” Baker, Jr. was an Okie. He was born in Yale, Oklahoma (home of Jim Thorpe) two days before Christmas in that grim year of 1929. His father, Chesney Baker, was a guitar-player, who idolized Jack Teagarden and Bix Beiderbecke. Chesney played guitar and banjo in the studio band at WMX radio. After work, he would often bring his friends back to the house to listen to jazz records and smoke dope, while little Chet fiddled around on a ukelele and an unwieldy trombone. As the grip of the Depression tightened, Chesney eventually lost his job at the radio station and skidded into a lingering despair that he tried to wash away with whiskey. Chesney got violent when drunk and regularly beat Chet’s mother Vera. Chet wasn’t spared his father’s wrath. “His father used to beat the shit out of him,” recalled Sandy Jones, one of Chet’s many lovers.

By 1940, the Bakers had given up on Oklahoma and joined the great migration west. Chesney left first, fleeing the household for California, where he landed a job at Lockheed. A couple of months later he sent two bus tickets for Vera and Chet. They eventually joined him in a small house in Glendale. By then Chet had picked up a trumpet. He seemed to be a natural. In 1946, Chet dropped out of high school and joined the Army. The war was over and Chet was shipped off to Berlin, where he played in the Army band, flirted with local girls, traded in black market goods, and goofed around amid the ruins of Germany. He was a wiry kid with the anodyne, unformed features of a pre-adolescent. Chet was out of the Army two years later, trying to study musical theory at El Camino College in Los Angeles. But Baker was so bored in the classroom that he soon reenlisted, landing a dream posting in the Sixth Army Band at the Presidio in San Francisco, where his primary military obligation was to play reveille and taps. In between, Chet was on his own, exploring the jazz clubs of the Bay Area, places like the Tenderloin’s Black Hawk and Bop City, the famous waffle shop / jazz venue on Post Street that hosted everyone from Billie Holiday and Lester Young to Louis Armstrong and Coleman Hawkins. One night at the Black Hawk young Chet sat in with Dave Brubeck and the great altoist Paul Desmond, with a young jazz-fiend named Clint Eastwood, skulking in the corner of the room.

But Baker was learning his chops mostly by listening to records, especially the early recordings of Miles Davis on 78s that would eventually become culled together into the landmark album Birth of the Cool. Baker was a gifted mimic, but never a stylistic innovator. He ruthlessly mined Davis’s phrasings, the soft, dark melodic lines, the terse, almost minimalist approach to the solos. “I didn’t really get locked into what I wanted to do until I heard Miles,” Baker told Downbeat a few years before he died.

For his part, Miles was never especially captivated by Baker’s playing. In 1963, Baker was performing at the Blue Note. He spotted Davis sitting in the crowd. Between sets Baker sauntered over to Miles’s table and gave him a salute. “Man, you suck,” Davis chuckled, shaking his head. Baker slunk away without saying a word, went backstage and shot up.

Chet Baker’s sound was a purified version of Davis’s ballad-playing, emotive and spare, which made it all the more appealing to the burgeoning West Coast jazz scene, which, headlined by players like Harry James, Artie Shaw, Buddy Rich and Art Pepper, was almost entirely white.

Years later Baker came to resent Davis and other black musicians. He deprecated Davis’ revolutionary second Quintet and his excursions into fusion. “They aren’t even songs,” Baker fumed. He couldn’t play the music and didn’t understand it. Chet was also an early proponent of the notion of reverse discrimination. He believed that music critics didn’t take white musicians seriously and that he was being denied gigs and record deals because he was white.

In 1952, Baker’s career took off when he was tapped to join a dissolute Charlie Parker for a series of West Coast gigs. Parker was the great innovator, the originator of bebop, the stoned visionary of a revolutionary new sound. He was also a helpless junkie, ravaged by a decade of almost unimaginable levels of opiate consumption.

When he hit the West Coast that spring, for the first time since being locked up in the notorious drug prison at Camarillo, Parker was a shambling ruin, drinking a quart of Hennessey’s every night, chewing Dexedrine like gum, prowling for smack every night. Chet Baker soon became Parker’s runner, driving down Central Avenue buying heroin to feed Parker’s enervating habit. Baker probably shot up for the first time with Parker, the Orpheus of addiction. Parker was generous with his dope and his praise. He said he enjoyed Baker’s playing, calling it “pure and simple.” Two years later Bird was dead and Baker was hooked for life.

Baker later mythologized his gigs with Bird, inventing a much-repeated tale about Parker returning to New York and chiding Dizzy Gillespie and Miles Davis about “a little white cat on the coast who’s going to eat you up.” But bootlegs of those performances at the Tradewinds and Tiffany Club tell a different story. Baker’s playing is timid and hesitant. He stumbles through his solos and seems lost in the cyclonic swirl of Parker’s sax. Even so, the dates with Parker conferred on Baker a kind of anointment; he had been blessed by a legend.

In the audience for those sessions with Parker was a young, gangly photographer from Pasadena named William Claxton. Claxton was obsessed with Parker, clicking photos of the band all night. But when he saw the images emerging in the dark room, it was not Parker who struck him, but the chiseled features and wind-swept hair of Chet Baker. In a city obsessed with the allure of images, Baker struck a captivating profile, emitting an aura as distinctive as any movie star. Claxton would photograph Baker for years, his stills charting the entropic decay of the trumpeter-junkie’s face. Call it the origins of heroin chic. Decades later, those early Claxton images would entrance the fashion photographer Bruce Weber, who became so enamored with Baker’s pallid visage that he tried to recreate the look in his shoots. Later, Weber spent more than a year making a documentary on the trumpeter, a strange, compellingly watchable film charting Baker’s final descent called Let’s Get Lost.

Baker was a hot commodity. Around town he became known as the James Dean of jazz. Hollywood celebrities, including Robert Mitchum, and Lana Turner, were dropping in to hear him play at places like the Lighthouse in Hermosa Beach, a venue that came to symbolize the new sound of the West Coast movement. Baker’s music in those days was airy and edgeless, featuring slow-paced beachside nocturnes, charged with a celluloid romanticism.

Off and on, Baker played with the tenor player Stan Getz in southern California clubs. Indeed, Baker’s first official recording was with Getz on a cover of “Out of Nowhere,” recorded live at the Trade Winds Club. Though they disliked each other intensely, Getz was also a junkie and he would often shoot up with Baker. In fact, Getz overdosed several times at Baker’s pad in West Hollywood. Baker recalled dragging the unconscious Getz into the bathtub and running cold water over him until he came out of it. At another party, Baker found Getz slumped in a heap, a needle stuck in his arm, his face turning blue. Baker and his pals spent an hour reviving the musician. When Getz finally came around, he snapped that Baker had “messed up my high.”

In the summer of 1952, Baker began his brief but intoxicating collaboration with the sax player Gerry Mulligan, who had landed in LA a few months earlier with his sax and a nasty habit. Baker and Mulligan couldn’t have been more different. Mulligan was tall, cerebral, a gifted arranger and songwriter with a deep knowledge of classical music and jazz history. He was mercurial and authoritarian. He was a reader and a dope addict, who first got popped by New York police in 1946. Mulligan was also something of a megalomaniac and control freak, who thought he was going to recast the sound of jazz by eliminating the piano.

Their relationship was fractious from the start with Baker storming out of the first rehearsal and telling Mulligan to “go fuck yourself.” But the Mulligan Quartet, with Baker on trumpet, Bobby Whitlock on bass and Chico Hamilton on drums, soon became one of the hottest acts in town. The band’s first gig was at the Haig, a small jazz club on Wilshire, where Erroll Garner was once the house piano player. In those early weeks playing together Mulligan and Baker created an intimate and smoky sound, more relaxed and melodic than the Birth of the Cool sessions. They complimented each other in surprising ways, tending to forgo soloing for playing duets or in smooth harmony. They played a mix of Mulligan originals and standards, none more famous than the Rogers and Hart ballad “My Funny Valentine,” which Mulligan had somehow excavated from the film Babes in Arms. Mulligan wrote new charts for the song, but Baker’s achingly beautiful, almost painfully deliberate solos turned the ballad into a dark classic of doomed love. “I believe Chet was kind of a freak talent,” Mulligan said years later. “There’s no figuring out where he learned what he knew.”

The band rushed into the studio to record an LP for the new Pacific Jazz Records. The album earned rave reviews and sold well. Movie stars, including Marilyn Monroe and Jane Russell, and directors came to hear them play and hang out with the band. “They were good-looking white musicians,” Mulligan’s girlfriend Jeffie Boyd said. “In LA, white was good. Black, people weren’t so sure how to take.”

Then Baker got arrested for smoking pot in his car. He got off lightly, only three months probation, but the police leaked the arrest to the press, trying to smear Baker’s reputation. Still the publicity only seemed to enhance his allure, especially for young women. Chet Baker may have been the first jazz musician with groupies. The women flooded to his gigs less for the music than to get a glimpse at his angelic profile. At the time, Chet was married to his first wife, Charlene Souder. But the trumpeter was soon hooking up with starlets, often in his car between sets. “It was girls, girls, girls for him,” drummer Larry Bunker told James Gavin. “He was fucking everything in sight, treating Charlaine like a piece of shit, balling chicks on the ten minute break out in the car while Charlaine was sitting in the club. That was his style.”

Though one of Baker’s lovers exalted his talent for cunnilingus (he was a trumpet player, after all), Baker’s sexual technique drifted far from traditional notions of romantic love. He had no interest in foreplay, didn’t like to kiss and basically wanted to have missionary position sex as quickly and harshly as possible. The sensual experience of being next to Baker also lacked a certain erotic appeal. Hygiene didn’t come high on Baker’s list of priorities. He didn’t like to bathe, wash his hair or brush his teeth—when he had teeth. He rarely changed his clothes or washed them. By the mid-1960s, he walked around in sandals, because his feet were swollen from repeated injections, his untrimmed toenails curling like a Chinese empress. Nearly all of Baker’s long-time lovers became heroin addicts, after they encountered Chet.

Baker was a beater. He would berate and slap and punch his wives and girlfriends, often in public. His wife Carol was repeatedly seen sporting a pair of black eyes. He tried to strangle his longtime girlfriend Ruth Young with a telephone cord and later broke into her apartment, looted the place and sold her grand piano to pay for drugs.

Groupies weren’t the only ones tailing Baker in 1953. He and Mulligan were also being watched by a pair of vicious LAPD vice cops, John O’Grady and Rudy Diaz, who had made it their mission—often unauthorized—to bring down jazz musicians. O’Grady was a racist thug who enjoyed terrorizing musicians, especially jazz players, who he viewed (like his hero Harry Anslinger) as degenerates and corrupters of youth. In his time, he stalked and busted Stan Getz, Billie Holiday, Lenny Bruce and Dexter Gordon. “I ran Charlie ‘Yardbird’ Parker, the great saxophonist, out of town,” O’Grady boasted in his revolting memoir O’Grady: the Life and Times of Hollywood’s No. 1 Private Eye. “I could have nailed him. His arms were covered with track marks from heroin needles. But he was too old and too drunk and I decided it wasn’t worth wasting the time nailing Parker just so the City of LA could pay for his keep.”

So the savage O’Grady set his sights on the hot young guns Baker and Mulligan. O’Grady and his thugs busted into Mulligan and Baker’s pad one afternoon while the musicians were rehearsing. O’Grady found a few pot leaves and stems and used it as a pretext to arrest Mulligan’s girlfriend, Jeffy, and Baker’s wife, Charlaine. The drug cops then tracked down Baker and Mulligan. O’Grady noticed fresh track marks on Mulligan’s arm, enough for an arrest in those day, and badgered the sax player into handing over his needles and a tiny amount of heroin. All four were hauled into jail. Eventually, Mulligan took the rap for the whole bust. He was sentenced to six months in prison.

Baker walked free. But the band was without a leader. Chet didn’t fill the bill. Baker knew the melodies, but didn’t know chords and often couldn’t even tell the band what key to play in. Soon Baker was matched once again with Getz. The two junkies still despised each other. Getz considered Baker a primitive musician and it grated on him that the crowds came to largely to gawk at the trumpeter. The partnership ended at the Black Hawk in San Francisco when Baker, who showed up late for the gig, stormed off the stage because the band had begun playing without him.

Still Baker’s star was rising. He was getting great reviews in DownBeat and other jazz publications. Several reader polls in the early 1950s even slotted Baker above Miles Davis and Dizzy Gillespie as best trumpet player. His early solo albums, Chet Baker Quartet,Chet Baker Ensemble and Chet Baker With Strings, sold so well that Baker decided he didn’t need Mulligan any more, even though Mulligan had taken the fall for Baker and his wife in the drug bust. “Gerry’s so pissed off because I’ve been able to make it on my own, without him,” Baker gloated in an interview. “He can’t hack that. I was supposed to be his trumpet player for life, I guess. And at ridiculous wages. He wouldn’t give me a raise, and I’d just been voted the best trumpet player in the world.”

Then Baker decided that he wanted to sing. He demanded that Pacific Jazz boss, Dick Bock, record an album of Baker singing ballads. Bock eventually relented. The album Chet Baker Sings, featuring eight ballads, including “The Thrill is Gone,” “My Funny Valentine,” and “I Fall in Love Too Easily,” was unlike anything else in jazz at the time.

The reception in the jazz community was unremittingly hostile. Even his bandmates hated the record. “I thought it was bullshit,” his pianist Russ Freeman told Gavin. “Total bullshit.” Mulligan wasn’t impressed either. “That’s just the way Chet sang,” Mulligan said. “He didn’t know any other way to sing.”

This was not Ella Fitzgerald or Louis Armstrong or Anita O’Day. There’s no scatting here. Baker didn’t bend, elongate or improvise his singing of the lyrics. Instead, Baker’s voice was flat, nearly emotionless, a dry monotone. The lyrics are slurred in a vibrato-less delivery that makes them sound stark and austere, songs of doomed love crooned by an automaton. You will search in vain for even a fragment of irony. Jazz musicians and critics may have recoiled at nearly every dreary chorus of Chet Baker Sings, but women and gays loved the record, driving it up the charts and adding another curious layer to the Baker legend.

In keeping with his other prejudices, Baker was something of a homophobe and his growing mystique in the gay community of LA and San Francisco unnerved him. He was determined to set the record straight. “There was a very mixed reaction when I started singing,” Baker said. “In the first place, a lot people thought – foolishly so – that because of the way I sang I, y’know, liked fellars or something. I can only say that that’s a lot of bullshit.”